


When the Timing is Right

by Winchester_with_Wings



Category: Supernatural
Genre: DO NOT COPY, DO NOT REPLICATE, Do Not Translate, F/M, Fluff and Smut, Oral Sex, Reader-Insert, Reader-Interactive, Smut, emotional because of how long you've been trying to get pregnant, personal request, request, trying to get pregnant, unprotected sex
Language: English
Status: Completed
Published: 2016-02-08
Updated: 2016-02-08
Packaged: 2018-05-19 05:35:56
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 1
Words: 5,168
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5955607
Author URL: https://archiveofourown.org/users/Winchester_with_Wings/pseuds/Winchester_with_Wings
Summary: <blockquote class="userstuff">
              <p>Requested by Anon: Can i request a reader and dean smut with some fluff in there about how much he loves her and they’ve been trying for a kid but with hunting its hard and after 3 years it finally happens</p>
            </blockquote>





	When the Timing is Right

**Author's Note:**

> This was requested by a reader who's been struggling to have a child with her husband for at least three years. I hope it happens for her soon.
> 
> I do not presume to fully understand the gravity of the emotions that go into trying to have a baby. So if it’s inconsistent with those kinds of experiences, I’m sorry.
> 
> *gifs are not mine and I know they’re different women but pretend they’re the same. Wasn’t sure which one to use.*

 

A Tuesday afternoon in January finds you so bored that you’ve resorted to cleaning up your bedroom and the bathroom, where you organize your toiletries.

Sam and Dean are out on a hunt and you stayed behind at the bunker for research. It’s been quiet all day so you’re hoping that they’re on their way back. You’re excited, of course. Always happy to see Sam and your boyfriend Dean returned unharmed, more or less.

Once you’ve organized one of the bunker’s several first aid kits, you mindlessly color code your nail polish, which you keep in a box under the sink. A particular shade of red and your bare toenails catches your eye. Before you even think to clean up the mess you’ve made going through the cabinet under the sink, you just sit down on the edge of the bathtub and start to paint your toenails.

As usual these quiet afternoons lead to you pampering yourself somehow. Last time, you took a ridiculously long shower where you washed, exfoliated and shaved everything so that you were squeaky clean and smooth. Then you took a nap in the bed you and Dean shared, the feel of the sheets running over your naked body was divine. Even though Dean had complained about there being no hot water for a shower, he had certainly appreciated the results.

Today, your skin is already well taken care of so all that’s needed is the nail polish. Such tiny luxuries make you feel like your life is normal. Though, of course, it’s not.

You, your boyfriend and his brother are hunters after all.

Dean’s more than a boyfriend to you, though. You’ve been together for almost five years. You’re basically married but since you’re hunters, you haven’t really had the big white wedding and living outside the law means a courthouse marriage wouldn’t matter or even be legitimate. But it’s never been a problem because Dean is 100% committed to you and you are to him.

As you finish painting your nails, you inspect them and wonder if Dean will notice. It used to be that Dean would roam and lavish every inch of your body. Back then he would’ve noticed, but now? The last time that you and Dean had sex, it was rushed and you two went straight from making out to the part where Dean came inside you. You tried to not take it personal since he was on his way out to meet Cas on a hunt that was time sensitive.

Just thinking about it though stings, so you try your best to push it away. You don’t want to feel like that, especially when he’s coming home soon and you can’t wait to hold him in your arms.

Walking carefully so that your toes don’t smudge, you go back to that cabinet and put away your nail polish. You start to sort through the medicine cabinet next, throwing away empty bottles of advil and other useless items taking up space. You condense your box of tampons by just throwing away the box and storing the few individual tampons in a drawer. You silently and bitterly remind yourself that the next time someone goes out for supplies, they’ll need to buy more for you.

There’s another empty box too.

It’s staring you right in the face, mocking you. Saying you should just forget about it and never buy another box like it again.

It’s not really empty, it’s full of pain, heartbreak, disappoint, frustration and downright anger.

You imagine that no one else would ever regard an empty pregnancy test box the same way. (Though of course there are plenty of couples who probably could sympathize.)

You and Dean have been trying to have a baby for three years.

More than two dozen pregnancy tests have been wasted on this endeavor. Actually, “wasted” isn’t the right word, though sometimes it feels that way. You’re still trying, after all.

You’ve had countless discussions on the topic. The first and foremost topic being why you both want to bring a child into a dangerous world that always needs saving. Sometimes, that idea gets to one of you and convinces you both to put the baby-making on hold. The sex doesn’t stop though, you just start using condoms again. Other times, it’s really just been bad timing. You’re both hunters and sometimes the fight comes first and a pregnant hunter would be a liability.

The idea of throwing away the empty pregnancy test box is laden with symbolism and a decision you’re not sure you’re ready to make. You’re still staring at it when Dean walks into the bunker a minute later and starts calling out your name.

“Y/N! I’m home! Baby? Where you at?”

He sounds excited and you wonder if it’s because of you? Is he really so excited to see you? Why? You look at yourself in the mirror, depressed and full of disappointment. A few tears silently fall down your cheek. You’re wiping them away when Dean bursts into the room.

He tosses his duffel bag on the bed, calling your name some more, looking around the room and finally finding you in the bathroom.

“Baby, hey!” he says with a big grin on his face and arms stretching out to embrace you. He trips up when he sees you wiping away the tears and trying to smile. “Babe? What’s wrong? What happened?” He gently cups your elbow and turns you into his body. You rest your head on his shoulder, breathing in the familiar smell of his musk and Irish Springs body wash. “Why are you so sad, Sweetheart?” he asks as he holds you.

He notices the empty box squished between your bodies and takes it from you with one hand. You don’t put up a fight. He stares at it for a moment too, with mossy green eyes, well versed in hiding sadness. He frowns at it before setting it down on the counter. He kisses your hair and then your forehead.

“Don’t worry, Baby. We’ll buy more,” he mutters, squeezing your shoulders. He inhales quickly and his mood changes. “Besides, don’t you know what day it is? I broke so many traffic laws to get back here in time. I’m outlaw for you, Baby.” Dean wiggles his eyebrows and smirks at you. It elicits a giggle from you as he speaks, cupping your cheek and making you look up at him.

“You’ve been an outlaw since before the day I met you, Dean Winchester.” Dean smiles proudly. “It’s a Tuesday. What’s so special about Tuesdays?” you ask, genuinely confused.

“Well don’t ask Sam that question,” Dean looks over his shoulder jokingly then wraps his arms around your waist. “It’s the first day of your ovulation isn’t it? Or is my calendar off?”

“You remembered?” You’d actually forgotten. The last time you’d looked at your calendar on the wall, it was when you’d changed it out for a new one and opened it up to January.

“I have an app for it. Sam found it for me. It tracks…” Dean looks down like he’s going to look at your belly but you’re pressed up against him so he just gets an eyeful of your bountiful pushed-up cleavage which seems to render him speechless for a second.

“Eyes up here,” you say, rolling your own eyes and giggling.

“Your…uh…lady stuff,” he finally finishes. “I love how they jiggle when you laugh,” he murmurs. Dean has always loved your breasts so his recent confession isn’t a surprise but it’s nice to hear. It boosts your confidence so you don’t even have to think twice about wearing low cut scoop neck shirts. You loop your arms around Dean’s neck and shimmy your shoulders a bit to make them shake again.

His goofy grin disappears and then your boyfriend is bending his head forward and squeezing you tight so that you’re on your tiptoes and he’s able to drop soft kisses along the top of your breasts and along your collarbone. His nose ghosts over your skin up your neck. He nuzzles you and his scruff tickles you, giving you goosebumps from head to toe. He inhales deeply.

“Mmm, you always smell so good,” he mutters against your throat. “Missed you so much, Baby.”

“I missed you too,” you say, running your hands up his arms and into his hair. You tug on his sandy blonde hair. “Hmm, we should wash your hair,” you whisper in his ear. You curl your fingers, starting to massage his scalp. Dean’s hygiene isn’t always a priority on hunts if all he has access to is a shower with terrible water pressure, no hot water, and no you. He rolls his head into your grasp and places a soft kiss to your increasing pulse.

“I love it when you wash my hair. Love taking you in the shower too,” he growls as he starts to suck a mark into your neck. Your head rolls back, exposing your throat to his wet kisses. “But not today. I want you in our bed.” Dean’s hands slide down to your ass like he’s about to move you from the bathroom to the bedroom. For some reason, your toenails come to mind.

“Oh hey, I just painted my toenails. Don’t mess them up.” Dean chuckles.

“I’ll try but I just love getting messy with you.” Dean coaxes you into standing on the toes of his boots. He starts giving you quick kisses like he’s more focused on walking when really he wants to be kissing you. He takes a few steps, backing out of the bathroom and turning to lean his back against the bedroom wall. The way he bumps into the wall makes you get off of his boots and take a step back. He gives this sort of breathy chuckle and starts looking you up and down.

The lust in his green eyes has darkened his stare and you think that maybe you see a hint of apprehension behind his gaze. Your combined attempts to conceive weighs heavy on him too and no matter the context of your love making, the intent of conception always lingers in the background.

“Do you want me, Dean? Do you desire me?” you ask in a shaky whisper, desperately reaching for a reassurance that no matter the outcome, you are still wanted by your lover. It’s something that you’ve always asked since you and Dean started sleeping together and then fell in love.

Dean notices this misty glaze in your eyes. He runs his hands up your hips, sides and arms. He squeezes your shoulders and his thumbs rub in soothing circles.

“Yes. Always. Forever and Always, Y/N,” he responds, the corner of his mouth tilting up into that reassuring loving smile.

Your face cracks with a small smile too as you slowly move your hands up his chest. Cupping the back of his neck, you pull yourself up to him. Dean’s hands tangle into your hair. He cradles your head with one hand and eventually moves the other down your back to keep you pressed against him as you slant your mouth across his.

His moans are joined with your own as your kisses deepen and become all-consuming. You crave Dean Winchester like he’s your life force; your source for all that is warm.

When he’s not around. your need for him is always simmering under the surface. And when he’s near, every touch sets your skin on fire. And he knows that. He loves titillating you with lingering and featherlight touches. And right now, Dean can’t keep his hands off of you. Your whole body is hot like molten lava. You can feel a flush rising up in your cheeks. That lava sensation melts away all of your concerns and refocuses all of your energy to the pool of arousal building low in your belly.

Dean had mentioned that he wanted you in your bed. But that clearly doesn’t mean you would be starting there.

A rumbling in Dean’s chest is met with him pushing the two of you away from the wall. He wraps his arm around your back and moves his left hand down to the back of your thigh. He bends his knees and makes you jump up so that he can wrap your legs around his waist.

His left hand is on your ass now, squeezing it and holding you up, and the other is splayed between your shoulder blades. His fervent kisses on your neck trail up to your jaw and then you’re the one swooping back in to claim his mouth. Your fingers curl into the nape of his neck as you cling to him desperately and try to prevent the kiss from never ending. You hate being apart from him and the ardor in which Dean takes control of this kiss suggests he feels the same way.

His tongue explores every inch of your mouth. He nips and sucks at your bottom lip and you do the same. Dean has the most amazing mouth and as much as you love kissing his luscious lips, you love having his mouth everywhere else on your body too.

He spins around so that now he’s got you pinned to the wall. He grinds his hips into you. His cock is already hard and knowing that he’ll soon be inside you only prepares you more. The heat and wetness you feel growing between your legs is dampening your panties and yoga pants. Can Dean feel that through his jeans?

Dean’s hand has moved from your back to the wall, caging you in. He tears his mouth away from yours and starts nuzzling your neck again. He nips and tugs at your earlobe.

“Mmmm, your skin is so soft,” he whispers. “Wanna taste and touch every inch,” he growls. “Wanna feel your skin against mine.” The hand on your ass actually slides into your yoga pants to cup your ass. The cool air on your skin tells you that he’s starting to pull off your pants.

Your legs release Dean’s strong, solid hips. You bare feet catch you and support you as you claw at Dean’s shirt.

“Then take off your clothes, baby,” you purr. He lets you pull his black t-shirt over his head and when your hands fly to his belt, he blocks you so that he can take off your shirt too. He keeps you pressed against the wall as he kneels down to peel off your pants. They’re tight and they require some tugging which he grumbles about and makes you giggle.

He slowly rises to his feet, sliding his hand up your leg. His hand cups your sex and if he didn’t know how wet you were before he knows now. His fingers start to rub through the thin lace, circling around your clit. The pleasure that jolts through you makes you whimper/ He quirks a smile at you and leans in to whisper in your ear.

“So wet already, baby? You couldn’t wait for me to come home, huh? Can’t wait to feel me inside you?”

“Mmhmmm,” you moan, tugging on Dean’s belt. His fingers retract and you want to complain but there’s no time as Dean scoops you up and carries you to the bed. He drops you on the bed spread and the way you bounce makes you laugh. But there’s no silly gleam in Dean’s eyes. The lustful stare he’s set on you is feral.

With a flirty twinkle in your eyes, you start to scoot your way up the bed. But Dean bites his lip and shakes his head. His fingers lock around your ankle and then he’s pulling you back down the bed. He hooks his fingers in your panties and pulls them down fast enough that you worry for a second that they might tear.

“Did you touch yourself while I was gone?” he asks, unbuckling his belt and kicking off his boots. You chew on your bottom lip to tease him. Of course the answer is no, because Dean satisfies you so often. You shake your head once Dean has shed his jeans so that he’s in his black boxer briefs, tenting with his hard cock. “I haven’t come since the last time we were together.” That’s means more than a week. He climbs onto the bed, his hands spreading your legs and putting yourself on display. “Don’t want to waste my cum…when it belongs inside you,” he murmurs as he lays between your legs. He kisses the insides of your thighs as his fingers start to tease your slick lips. Skipping just the one, he slides two fingers inside you and hums with satisfaction. “Mmmm, you’re so ready for me, huh, Y/N.”

He starts to move them in and out of you and when he curls his fingers, your back arches off the bed and you gasp. You sharp intake of breath turns into a moan as you bury your fingers his Dean’s hair. The moment his mouth and those luscious lips close around your clit, you’re gone. He sucks and twirls his tongue around the sensitive nerves and when that’s combined with his fingers pumping in and out of you, you crash headlong into a orgasm that has you pulling hard on Dean’s hair.

He doesn’t react like the hair pulling hurts him. In fact, you maintain that Dean Winchester likes having his hair pulled when making you come. He’s even smiling as he retracts his fingers and licks a line up your slit, his tongue catching on your entrance. It makes you twitch with a shock of pleasure and Dean chuckles and hums as he kisses your clit.

“You like that, baby? Like it when I make you come?” Dean’s strong, tan arm reaches up to cup one of your breasts. You arch into his touch and look at him, buried between your legs. He pushes up to drop several kisses on your tummy.

“Mmmhmm,” you respond, your heart is racing and you’re too breathless to say much more. Dean’s fingers slide into you once more and slowly stroke you as he gets onto his knees and starts to take off his underwear.

Once his dick is free, you reach out for it and start to stroke it. Dean’s up on his knees so he pulls out his fingers and licks them as you sit up. You’re level with his cock now. While making eye contact with him, your tongue flicks out to catch his pre-cum and then you’re wrapping your lips around the head. Dean’s eyes close as the wetness of your mouth envelops his cock. His head falls back and his mouth hangs open.

“Ohh, fuck baby,” he groans. His fingers thread into your hair and when you start to suck and take in his length, he only lets you bob two or three times. His grip suddenly tightens in your hair and his hips twitch. He pulls your mouth off of him. “Mmph, fuck, Y/N, babe! You can’t do that or I won’t last.” You giggle and allow Dean to push you down onto the bed.

Dean grabs a pillow and puts it up your hips. You’re both well versed in the best positions to conceive and they all feel amazing.

You take a hold of his cock and stroke it as you line it up with your entrance. Dean’s hands grab the back of your knees and as he lifts your legs, he kisses his way to your ankle.

“I love the color you picked out,” he comments when he looks at your toenails–which are hopefully dry now. To thank him, you run the head of his cock up and down your slit, slicking it up. His nose crinkles and his nostrils flare as he casts you a wickedly sexy glare. Keeping his hands wrapped around your ankles, with your guidance, Dean pushes into you. He goes in slowly, stretching you and bottoming out made easier with your arousal. “Fuck, you’re so tight.” Going for almost two weeks without him does that.

Dean goes as deep as possible. He starts to thrust, a few times he pulls almost all the way out and then drives back in. He keeps your legs up and hooks them over his shoulders as he looms over you.

The two of you are a combination of tangled limbs, a symphony of moans and murmured ‘I love yous’. Both of you have your eyes closed but you know every inch, every curve of your bodies, sleek and glistening with sweat.

Dean’s hands aren’t on your legs anymore. He’s massaging your breasts with one hand and rubbing your clit with the other.

“Come for me, baby, wanna feel you come,” he mutters, pounding hard and deep into you, rocking into you to your very core. He leans in to kiss you but you tear your lips away from him as you shout his name, climaxing so hard that you feel like you’ve been struck by lightning. Your whole body convulses, hips bucking and coming up to meet Dean’s hips as he slams into you. “Ohhh god, fuck, baby, I’m gonna come. Gonna come inside,” he grunts. His hips move erratically but he’s so deep you can feel him striking your inner walls. He needs to be this deep too. That’s what the position facilitates too. His thumb rubs hard on your clit this it almost hurts but the combination of pleasure and pain makes more lightening erupt behind your closed eyes as you orgasm with him.

When Dean comes, his back stiffens and he goes to the very hilt. His hot seed empties into you and you orgasm milks him for everything he’s got. Dean releases your legs but the pillow underneath your hips has you tilted enough that it should still help.

Dean gently collapses on top of you, panting. He kisses your forehead, your cheeks and you lips. You caress his face, running your thumbs over his freckle-dusted cheekbones.

“You’re so beautiful,” he whispers, wiping away some of your hair from your brow.

“So are you,” you chuckle. Internally, you almost think to say a silent prayer, hoping that you’ve just made a baby but you don’t want any angels to hear that and you don’t want to take away from the time you and Dean just shared.

After a minute, when Dean has softened a bit and caught his breath, he pulls out. He makes sure that nothing else does, adjusting the pillow under your hips to lift a little higher. He lays next to you, propping his head up with his hand.

“So I kinda pounced on you the moment I came home. How are you? How was your day?” Dean smirks and chuckles at you as you roll your eyes and laugh.

“It got much better when you came home,” you say sincerely, rolling your head to the side to look at him. “I missed you. And I missed this,” you gesture between yours and Dean’s naked body and giggle.

“Well that’s good, because I’ll be _recharged_ and ready for round two in less than ten minutes,” he winks at you before letting his head fall back onto the bed. You take a couple of deep breaths, probably thinking too hard about how he’s already expecting to have a round two. Yes, you two love to have sex and you never just do it once in one session but that pregnancy test box you came across earlier is still in the back of your mind, taunting you into overthinking.

“We don’t have to do it again if you don’t want to,” you say, giving him a chance to bow out. Dean frowns and sits up.

“Of course I do. I always want to go again, you know that, Y/N.” Dean rests his hand on your thigh to reassure you. “Plus, since you’re ovulating shouldn’t we have as much sex as possible? With enough breaks, I can have sex with you all day, like it’s my job,” he quirks his eyebrows at you and grins. It fades a little the longer he looks at you.

“I don’t want it to be your _job,_ Dean. I don’t want you to make love to me out of obligation, like it’s just a means to an end,” you say, laying your forearm over your eyes to hide your misty eyes. Dean pulls your arm away.

“Y/N, babe, I just joking. I love you. I love you so much. That’s why want to make love to you. We can even wear a condom if you want. I’m willing to do anything to prove to you that I love you, no matter what,” Dean says in his deep, soothing voice. He starts running his fingers through your hair. His brow is furrowed with concern and love and to see him looking at you with those emotions he’s vocally expressing, melts your heart. You feel guilty for questioning his motives but it’s hard to keep up the optimism. “Y/N, I just want to give you the baby you so desperately deserve. I want to start our family. I want you to be happy.”

“I am happy, Dean. I have you,” you say, caressing his cheek. He reciprocates with the same gesture, wiping away one tear. “It’s just…looking at the calendar…it’s January. It’s a new year and I’m worried that it’s just another year of _trying_ to have a baby. Do we give up?”

“No. I don’t want to,” he says, a muscle in his jaw twitches with his determination. “Do you want to stop trying?” There’s a hint of disappointment in his eyes because Dean wants this just as much as you.

“No. Never.”

“Then we won’t. And the next time I go to the store, I’ll buy two more boxes of tests, if that’s what it takes.”

 

* * *

 

Three weeks later, you and Dean are still trying. You’re both still happy as ever, enjoying each day, satisfying each other like there’s nothing but your pleasure on the line.

You haven’t taken a test since that first day of your ovulation. Dean hasn’t mentioned it, letting you know your body and make the decision when it’s time to take it. You don’t feel any different so you assume that the test will be negative anyway and you don’t want to put yourself and Dean through that.

You’re in the bedroom, folding laundry when Dean comes in. He comes up behind you, wraps his arms around your waist and kisses the back of your neck.

“Hey Baby,” you say sweetly.

“Hey, Sweetheart. I have something for you.”

“A present?” you respond with excitement. You turn around in his arms and Dean releases you for a second to pull something out of his back pocket.

He holds up the pregnancy test right between your face and his.

Your smile falters for a second and he notices.

“Sweetheart, I think you should take it. It’s been a while,” he says, shaking it to encourage you to take it from him. You do and he smiles, kissing you on the forehead. “I’ll be right here,” he says as you head for the bathroom.

You return before the test has a result. Your stomach is fluttering with nervous anticipation, building up and preparing to fall.

Dean’s finished the laundry and is sitting on the foot of the bed. You hand the test to him and show him the timer you’ve set on your cell phone. You’ll both see the results together.

“Maybe we should have Cas check on me again. Touch my stomach and make sure there’s nothing wrong. Maybe have him test you too,” you suggest absentmindedly as a distraction.

“No. I don’t think so. He did that a while ago and nothing could’ve changed since then,” Dean replies without taking his eyes off the test.

“You sure we should keep trying? Should we stop?” You ask (yourself) this question almost every time you think about getting pregnant and sometimes you meet it with optimism and sometimes pessimism. Dean’s more optimistic so you like it when he answers.

“Yes,” he says iN a firm but sort of distracted voice.

“Yes, what? We keep trying or stop?” you shrug.

“We stop,” Dean says in a voice that cracks like he’s going to start crying. Your heart skips a beat and your stomach flips. You feel like you’re going to throw up. Why would he suddenly change his mind?!

“Why?”

“Because it worked.” Dean holds up the pregnancy test which displays two red bars. “You’re pregnant, Y/N. _We’re_ pregnant. We’re gonna have a baby!” Dean’s grinning like a child on Christmas morning and a few tears of joy seem to be falling freely.

“Oh my god,” you say with your mouth hanging open in shock and happiness. Dean drops the pregnancy test and pulls you to your feet so that he can hug you and spin you around. You cling to him for dear life. Can this be? Is it really true? You start crying your own tears of joy, burying your face in Dean’s chest.

“Sweetheart, you’re happy right?” he asks, pulling your face out of his shirt and cupping your cheeks. His smile is glued to his face and his green eyes are bright and full of life.

“Of course I am! Dean, it’s positive! We’re gonna have a baby,” you smile, laugh and cry at the same time.

“We are, Y/N! This is why we never give up,” Dean starts kissing your face, starting with your forehead and cheeks, “Winchesters never give up,”  and then your eyelids, “And you’re a Winchester,” then your jaw and finally your lips. “And so is this baby,” Dean says resting his hand on your stomach. He gets on his knees and hugs your waist, resting his head on your tummy. “We just needed to keep trying and I knew that when the timing was right, it would happen.” You rest your hand on top of Dean’s hand and thread your fingers through his hair.

“We’re finally starting a family, Dean,” you say in a cracking voice, just barely keeping it together.

“We’ve always been a family, Y/N. Now it’s gonna grow.”

“I can’t wait to tell everyone,” you grin.

“You’re pregnant?!” Sam exclaims from where he’s standing in the open doorway.

“Well that’s practically _‘everyone’_ right there,” Dean laughs, still holding on to you. You nod and Sam beams at the two of you.

“Congratulations! It’s about time, too. I’m so happy for you guys!” Sam says as he enters the room. Dean gets to his feet just in time for Sam to envelop you both in his embrace. You can’t help but think to yourself that yes, this is already a family but a child–your child, with Dean Winchester–will be the perfect addition.


End file.
